Nov 182003

My girlfriend is a bit crazy for anal. When we’re out shopping at the mall, in broad daylight, with no concern for who hears her, she’ll say something like “I’d like that up my ass.” She will say this about video game controllers, sports equipment, household appliances, children’s toys — you name it. I think she gets a kick out of this. I just imagine the look on people’s faces when they overhear it, and I cringe. It’s embarrassing! She just doesn’t care. Would you recommend threatening to take away anal from her? Should I just end the anal ritual altogether? Or, God forbid, should I fuck her ass so hard that she never wants to do it again?

–I Have an Anal-Crazed Girlfriend

I can’t decide why I chose to answer your letter: to illustrate that I receive some of the best letters in the sex advice business or to indulge you because you might just be fucking with me! I’m going to embrace the former, and assume that your girlfriend’s behavior is, in fact, an issue.

First, all the men out there who can’t get their wives to agree to anal play at all are reading this and shouting out loud, “Dude! I wish I had your problems!” Count your blessings that you have not just a willing, but a clearly enthusiastic, anal sex partner.

It sounds to me like your girlfriend is not simply “anal crazed,” but she’s also a verbal exhibitionist: she enjoys saying bold, sexually suggestive things in public, and she wants those around her to hear her and be shocked. There is only one potential problem with this situation: there are many public places where it’s really inappropriate for her to talk her tushy trash, especially when she’s within earshot of children. Threatening to “take away anal” or actually doing that will only fuel her bratty inner-schoolgirl and hurting her during anal sex is just mean and stupid. Let her know that her explicit public chat bothers you, but also offer a solution: encourage her to save all her naughty little ideas for when you get into bed, where she can whisper them to you or shout them out loud. In that erotic context, you too will probably get off on her mouthing off. If she can’t keep her thoughts to herself the next time you go out, then a spanking and a gag are in order.

Jun 302003

My boyfriend frequently plays with my ass and I love it. We enjoy using everything from fingers to plugs to dildos. His only complaint is that my use of poppers is a real turn-off. He hates the smell and doesn’t like its effects on me. He says it creates distance between us rather than closeness. I experience it as greatly enhancing my tenderness and receptivity. It makes me open up and feel very submissive towards him and highly orgasmic. I feel very fortunate to have such a loving and adventurous partner, but I’m upset that he doesn’t understand this aphrodisiac and is unwilling to explore its potential benefits for both of us.

–Misunderstood Huffer

You’re not alone in your love of poppers. Also known as Amyl Nitrate or Butyl Nitrates, poppers are illegal drugs which people often inhale to enhance sexual pleasure. Poppers cause vasodilation, a widening of blood vessels which increases of blood flow. Amyl Nitrate relaxes muscles, which can help make anal penetration easier and enhance orgasm for some people. Lots of gay leatherman are big fans of using poppers as part of their anal play.

However, I agree with your boyfriend. Poppers — and drugs of any kind, for that matter — may cause you to relax and lose inhibition, but they also alter your physical and emotional state which may cause you to disengage from your partner. Poppers are not actually an aphrodisiac, although they may feel like it to you. I’m a fan of drug-free anal play, where both partners can be present, connected, and in touch with their bodies.

Apr 302003

My boyfriend and I have a Dom/sub relationship (he is the Dom). We also play with some “special friends” from time to time. Since I feel no hesitation having anal sex with him because of our love and trust, I am not really interested in engaging in it with others. He seems to see this as resistance to his control and it has led to some heated discussions. I have told him I am not interested but his challenge is, “How do you know you won’t like it if you don’t try it?” Do you have any advice on a good response or two that I can have ready the next time the subject comes up?

–Stubborn Submissive

While I understand that complete control and surrender of one’s free will is a goal for many people in Dominant/submissive relationships, I’m also practical: very few human beings can be 100% submissive and surrender all their free will to another person. That’s why it is quite common in the leather world for people to negotiate ground rules in scenes and relationships. I appreciate your Dominant’s desire to have your complete obedience, to push you to expand your erotic horizons, and to see other people fuck you in the ass; however, I am siding with you on this one. You have communicated a clear boundary to him, and I think that boundary needs to be respected. He needs to see that you having limits does not mean you are resisting him, but that you are taking care of yourself, listening to your instincts, and communicating clearly — which are all great qualities for a submissive to have.

Mar 282003

I’m a girl who likes to indulge in many different forms of erotic play, including: spanking, enemas, assfucking, bondage, fisting (vaginal and anal), S/M, and play piercing. I was introduced to these in college when I was 19, and have been enjoying them for years (I am now 29). Unfortunantly, my girlfriend refuses to participate in any of my fantasies. I live in a small city with my girlfriend where it’s impossible to meet anyone who enjoys ‘out of the ordinary fucking’ (traditional, man/woman, dick into pussy fucking). There isn’t even an adult toy store! I love her very much, but I constantly feel restless and incomplete when it comes to our sex lives. I don’t want to leave her, but I want to be able to satisfy my sexual needs. I’ve tried talking to her, but she won’t change her mind. I honestly don’t know what to do and would like an outside opinion.

–Love or Lust?

Your problem is more common than you might think because it boils down to this: you and your girlfriend are sexually incompatible. You tend toward experimentation, SM, and kink, where she sounds like she prefers a straightforward vanilla sex life. First know that sex and sexual compatibility are valuable, important aspects of a relationship, and the fact that you make them a priority doesn’t make you shallow or wrong. If your partner will not meet you half way and even try some of these activities with you, then you have two options: negotiate to open your relationship, so that you can explore your desires and fantasies with other partners or find a new girlfriend.

Nov 262002

My boyfriend and I have been going out for 5 years. My boyfriend wants to have anal sex, but he is very big and thick. He hurts me when we’re just having regular sex. I don’t know why, since I’m 100% wet when we have sex, and it still hurts. We tried anal once but I told him to take it out because it hurt even when he put the head in. I’m just afraid that if we have anal sex he’s gonna hurt me. He says he will go slow, but he never listens to himself. Just before he’s getting ready to cum he starts to do it harder, so I don’t know if I should do it with him or not.

–I Want A Pain-Free Poke

First, I recommend you really focus on extended foreplay before your boyfriend even attempts penetration with his dick. Have him go down on you, rub your clit, use a vibrator, and work your body before getting inside it. The more aroused you get, the better your circulation; blood rushes to the genitals, the body relaxes, the pussy lubricates, and penetration becomes much easier. You say you are 100% wet, but I still really recommend using lube. Lube makes everything nice and slick, and eases penetration whether he’s well endowed or not. You also need to warm up both your ass and pussy with something smaller than your husband’s dick, like his fingers or a smaller dildo or vibrator. Start small and slow, and work your way up. Add another finger or go farther in only when you feel completely relaxed and ready for more. Don’t rush it.

Once you start having intercourse, make sure you are in the driver’s seat. You call the shots about how hard, how deep, how fast. Talk to your boyfriend and make sure he knows when something feels really good and when it does not. Penetration, whether vaginal or anal, should never hurt you. Take the time to make sure your body is warmed up, you are ready, and make sure he’s connected to you so he knows when the time is right.

For some men, in order to orgasm they need to take some very quick hard thrusts, which sounds like it may be the case with your guy. If he simply can’t slow down or when he does slow down, he can’t come, then I suggest this: when he’s ready to shoot, have him pull out. Then you can give him a hand job, he can jerk himself off, or he can thrust against you but not inside you.

Jun 072002

My girlfriend and I have been having anal sex for about four or five months. In fact, the first time I penetrated her was anally. After that, it’s been a once-in-a-while ritual where I get to have the pleasure of making love to her sexy ass. I enjoy it very much and she doesn’t mind letting me have my way, even though she says she receives little to no pleasure from it. We use plenty of lube and always warm up with shallow and slow penetration, deep breathing and lots of communication. We now do it now once every three weeks to a month, which is kind of my problem. I’d like to do it more often, but not too much.

I have two questions for you: How much anal sex do you think is healthy for a couple that wants to have a nice balance between the three major forms of sex (oral, vaginal and anal)? What kind of ways can I pleasure her when I do her in the ass? How can I make her come from anal sex?

–Booty Lover

There is no mathematical equation to determine “a nice balance,” nor is there any common recommendation about how much of one kind of sex a healthy couple should have. Sexuality and our particular practices are extremely unique to the individuals involved, and therefore so are our preferences and how often or little we indulge in them. I say if both you and your wife are content with how much sex you’re having, and the kinds of sex you’re having, then why mess with a good thing?

But it does sound like you’d like to add more anal sex to the menu, and your second question is the key to getting there. Because if you start to give her tremendous pleasure while you’re fucking her in the ass, then chances are she’ll want to do it more often. There are a number of ways to get a woman off while you’re fucking her ass. You can play with her clit while you penetrate her, or if the position you’re in makes that too difficult, encourage her to jerk herself off or even use a small vibrator. Clitoral stimulation combined with anal penetration is one of the ways some women can orgasm. If she likes double penetration, try putting a few fingers in her pussy or a slim dildo while you’re in her ass; this often increases the sensations in both places. Experiment with different positions in order to find her G-spot. Many women experience indirect G-spot stimulation through anal sex. You want to angle fingers, toys, or your cock toward the front of her body to find and stimulate the spot. Also, ask her what she’d like to do to make it feel not just better, but fantastic. Together, you can discover what will turn you both on.

May 282002

My husband and I want to try out anal sex really bad, but my problem is the pain — I know it’s not supposed to hurt, but it does. I keep telling him that missionary position is not the best for our first try. Is there another position you recommend? I really want to give this to him, but I am still very nervous. I have tried to relax, but nothing seems to work. I’m thinking I need a lube that desensitizes the area. I know if I can find the right kind of numbing agent, then I will do just fine. Do you know of any?

–Anal Chicken

You admitted being nervous about getting fucked in the ass, which is very common, but my question is: do you really want to do it? I sense a lot of reservation in your letter, and I am concerned that your fear and anxiety aren’t the only things holding you back. Your desire for this must absolutely be there (not just your husband’s), otherwise it’s not going to work, and it will continue to hurt. You are right that it is not supposed to hurt, and pain can be the result of many things: hesitation on your part; not being relaxed; not enough foreplay and warm up; not enough lube. You need to take it slow, and have him open your ass with fingers or small toys before he even attempts to put his cock in there.

As for positions, if missionary isn’t working for you, trust your instincts. Maybe you should get on top, so you can control the depth of penetration, the speed, and you can move your body to get the best angle. Or you could try doggie style, but make sure he doesn’t thrust all the way inside on the first time around.

I cannot recommend any of the de-sensitizing lubricants that are available. Numbing your ass just isn’t a good idea. If you can’t feel anything, you cannot listen to your body’s warning signs that things are going too fast, and you’ll most likely end up with a sore butt the next day. Plus, if it’s numb, you can’t feel all the pleasurable sensations that anal sex can give you, and trust me, you want to feel those.

Jun 202001

Since I have been old enough to jerk off, I have been attracted to exceptionally buff and athletic women. The first time I ejaculated, I was fourteen and I was watching women’s gymnastics in the summer Olympics on television. Since then, I have desired a non-stereotypically-feminine woman. As my sexual development progressed, I discovered that I wanted such a woman to sodomize me—to fuck me in the ass with a strap-on. I have thought long and hard about this. Buff, athletic women are the most amazing, sexy creatures on the planet.

The desire has remained totally unsatisfied throughout my life. Recently, though, I was able, through some miracle, to go on a couple of dates with this girl who is on the diving team of my university. She is my ideal woman, and I really like her, but I’m afraid if I ask her for anal sex, I will lose a relationship with the sexiest, coolest, sweetest girl I have ever had the chance to be involved with. Help! How do I find out if she would be into anal sex with me? And, if not, how in the world will I ever find another as buff and beautiful as she is that might just be into anal sex with me? This girl is amazing, and I don’t want to lose her, even if that means sticking my thumb up my ass while thinking about her, and settling for strictly vanilla sex with the girl of my dreams.

—Buff Girls Rock My World

Well, it sounds like you really like athletic, assertive, maybe even butch, heterosexual women. I commend you for figuring out the unique type of person that floats your boat (and obviously gets your dick hard). As for seeing if she’s into fucking you in the ass, well, I think you need to take the plunge and ask her. I understand that you don’t want to lose her, but you also want to have your anal desires fulfilled, and those anal desires seem pretty fucking strong to me. So, approach her honestly and in a non-confrontational way, and tell her what you want. Hopefully, she will make all your dreams come true, and strap it on.

Mar 052001

I dated a woman for three years. We had a wonderful, rich, loving sex life. We had a lot of anal play, and we both enjoyed giving and receiving. I am ready to start dating again, and I am worried about anal sex. I like it, but I know not everyone does. I have been told (and I know it is true in my case) that a lover who really cares about me will want to fulfill my sexual desires, but the idea of “pushing” anal sex on anyone makes me nervous. At the same time, I like it.

When I dated this woman, we started slow and gentle (and very caring), and after a year or so, we were using handcuffs, talking nasty — for fun. I want to love a person first, and the sex second, but I am afraid I won’t get what I want. I have a feeling you are going to tell me that I am reasonably normal, and that I shouldn’t worry about it. If that is the case, fine, but I need to be told by someone knowledgeable in the field.

—Loving Anal Slut

You’re right, you are a reasonably normal guy, a reasonably normal guy who happens to really like anal sex. It sounds like your three-year relationship was very fulfilling for you, and that you approached anal sex in the right way, with plenty of love, communication, and patience (and lube, I hope!).

I think it’s absolutely okay that you want anal sex to be a part of your next intimate relationship. Your desire for buttfucking is obviously part of what makes you tick sexually, and bravo to you for identifying it and owning up to it. But I see your dilemma: what if you find the perfect girl and she’s not gung ho about you doing her bunghole? Well, presumably you are looking for a mate who has a similarly liberal and adventurous attitude about sexuality as you do; if you like anal play, bondage, and dirty talk, you obviously need a partner who’s inclined toward experimentation beyond the missionary position. As you date and hunt around for a new relationship, be confident in who you are and what you like, and be honest with your partners. I find that since I’ve gotten seriously into anal sex, I have not landed in bed with anyone who isn’t into some backdoor lovin’. I’m obviously putting some kind of vibe out there that people are picking up on, and I find that I tend to be attracted to people with whom I am very sexually compatible. Rather than feeling worried, obsessed, or even a little guilty about your anal desires, why not embrace them fully? Once you do, you have a greater chance of attracting women who will not only fulfill your desires, but may even exceed your wildest expectations!

Jan 072001

My wife and I have not delved into anal sex. She’s hesitant, while I’d like to play. I’d like us to play both ways, hers by me and mine by her. I’ve read your advice before and get the gist of how to do things. I need to open the conversation about anal in an attractive and fun way. Any suggestions on how to talk about what would be a new sport for us?

—Wanting to Play Ball

Well, I am glad to hear that you are already approaching the subject with an open mind and ass — mainly, that you’re willing to go both ways when it comes to anal pleasure — and I am sure your wife will be, too. Obviously, I want to let the world know about how awesome anal sex can be, but, as a sex educator, I don’t want to coerce anyone into doing something they don’t want to do.

You wrote that your wife is hesitant — have you talked about this subject with her? An honest discussion may be what both of you need. There could be a variety of reasons why she’s not gung-ho about anal sex. Like so many of us, your wife may have certain misconceptions about buttfucking — that it’s dirty, painful, or only for a man’s pleasure — which prevent her from wanting to dive right in. You should correct those myths with the facts: anal sex doesn’t have to be a big mess; if you do it right, it won’t hurt; and women can get off on it in plenty of ways.

Or, perhaps she has had a bad experience in the past. If a boyfriend before you tried to go from zero to 60 in five seconds by sticking his dick in her ass without warm-up, lube, or communication, then chances are it hurt a lot and she never wants to do it again. Here’s your chance to reassure her that this time, with you, it will be different. You will take your time, use plenty of lube, and work her ass up to your cock. If you want to be sexy about this whole conversation, why not whisper in her ear a fantasy you have about fucking her in the ass. That, coupled with communication and information, ought to get her revved up!